US6306894B1 - Injectable composition - Google Patents

Injectable composition Download PDF

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Publication number
US6306894B1
US6306894B1 US09/563,969 US56396900A US6306894B1 US 6306894 B1 US6306894 B1 US 6306894B1 US 56396900 A US56396900 A US 56396900A US 6306894 B1 US6306894 B1 US 6306894B1
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United States
Prior art keywords
composition
paclitaxel
pharmaceutical
acid
matter according
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Expired - Fee Related
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US09/563,969
Inventor
David Carver
Timothy Prout
Hernita Ewald
Robyn Elliott
Paul Handreck
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Mayne Pharma USA Inc
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Tapestry Pharmaceuticals Inc
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Application filed by Tapestry Pharmaceuticals Inc filed Critical Tapestry Pharmaceuticals Inc
Priority to US09/563,969 priority Critical patent/US6306894B1/en
Priority to US09/970,558 priority patent/US6770670B2/en
Application granted granted Critical
Publication of US6306894B1 publication Critical patent/US6306894B1/en
Assigned to MAYNE PHARMA (USA), INC. reassignment MAYNE PHARMA (USA), INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: NAPRO BIOTHERAPEUTICS, INC.
Priority to US10/835,875 priority patent/US20040204479A1/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12—Carboxylic acids; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin

Definitions

  • This invention relate to a solution of paclitaxel having improved stability.
  • Paclitaxel is a compound extracted from the bark of a western yew, Taxus brevifolia and known for its antineoplastic activity. It is described for example in The Merck Index, Eleventh Edition 1989, monograph 9049.
  • paclitaxel was chosen for development as an antineoplastic agent because of its unique mechanism of action and good cytotoxic activity against IP implanted D16 melanoma and the human X-1 mammary tumor xenograft.
  • Paclitaxel is believed to function as a mitotic spindle poison and as a potent inhibitor of cell replication in vitro.
  • Other mitotic spindle points (colchicine and podophyllotoxin) inhibit microtubule assembly.
  • Paclitaxel employs a different mechanism of action since it appears to shift the equilibrium of polymerimization/depolymerization toward polymer assembly and to stabilize microtubules against depolymerization under conditions which would cause rapid disaggregation of microtubules.
  • the interference with the polymerization/depolymerization cycle in cells appears to interfere with both the replication and migration of cells.
  • paclitaxel After extensive preclinical screening in mouse tumor models, paclitaxel entered clinical trials in 1983. Over the past few years, paclitaxel has demonstrated good response rates in treating both ovarian and breast cancer patients who were not benefitting from vinca alkaloid or cisplatin therapy. It has also shown encouraging results in patients with other types of cancer including lung, melanoma, lymphoma, head and neck.
  • the invention provides a solution containing paclitaxel, cremophor ELTM and ethanol, characterized in that the pH of the solution has been adjusted into the range 1 to 8 by addition of an acid.
  • Acids in the form of powders for example citric acid
  • those which contain water for example sulfuric acid.
  • the most preferred acid for use in accordance with the present invention is citric acid, but a wide range of acids may be used including the following:
  • Citric acid monohydrous
  • Paclitaxel is usually prepared and administered in a vehicle containing cremophor ELTM (a polyethoxylated castor oil which acts as a solubilizer) and ethanol.
  • cremophor ELTM a polyethoxylated castor oil which acts as a solubilizer
  • BMS Bristol-Myers Squibb
  • the invention essentially teaches addition of an acid to a paclitaxel formulation to adjust its pH into the range 1 to 8, preferable 5 to 7.
  • Citric acid was dissolved in absolute alcohol, using a ratio of 8 mls of absolute alcohol to 1 gram of citric acid, and the solution was stirred for fifteen (15) minutes.
  • Cremophor EL was weighed out into the main mixing vessel.
  • Solution 1 was added to solution 2, and the container used for solution 2 was washed with a minimum quantity of absolute alcohol to ensure complete transfer of the citric acid.
  • Solution 3 was mixed and bubbled with nitrogen for at least 15 minutes.
  • the paclitaxel was weighed out and slurried using absolute alcohol, using a ratio of 8 ml of absolute alcohol to 1 gm of paclitaxel.
  • the slurried paclitaxel was added to solution 3 and the slurrying vessel was washed with a minimum quantity of absolute alcohol.
  • Solution 3 was adjusted to 75% of required volume using absolute alcohol, and thoroughly stirred for at least 45 minutes until completely dissolved. Once completely dissolved, the volume was checked and made up as necessary with absolute alcohol and the final solution stirred for 5 minutes.
  • Cremophor EL 0.5 mL Citric Acid (Anhydrous) 2.0 mg Paclitaxel 6.0 mg Absolute Alcohol to 1.0 mL
  • the solutions were filled into clear type 1 glass 5 mL vials and sealed with rubber bungs.
  • the solution was filled into clear type I glass 5 mL vials and sealed with rubber bungs.
  • the solution was stored at 40° C. for 7 days.

Abstract

A pharmaceutical formulation of paclitaxel and polyethoxylated castor oil is disclosed to be relatively acidified to a pH of less than 8.1 and preferably within a pH range of 5 to 7, inclusively. Ethanol is optionally included in the formulation which is adapted for use in a body for the treatment of cancer. A formulation method is disclosed and includes the step of mixing an acid with a carrier material, such as polyethoxylated castor oil, to form a carrier solution after which paclitaxel is added in an amount such that the resulting pH is less than 8.1 and preferably in a pH range of 5 to 7. Ethanol may optionally be slurried with the paclitaxel before mixing with the carrier solution. A variety of acidifying agents, a preferred one being anhydrous citric acid, are described.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS
This application is a continuation of U.S. Ser. No. 09/356,158, filed Jul. 19, 1999, now U.S. Pat. No. 6,140,359, which is a continuation of U.S. Ser. No. 08/979,836, filed Nov. 26, 1997, now U.S. Pat. No. 5,977,164, which is a divisional of U.S. Ser. No. 08/594,478, filed Jan. 31, 1996, now U.S. Pat. No. 5,733,888; which is a continuation of U.S. Ser. No. 07/995,501, filed Dec. 22, 1992, now abandoned.
This invention relate to a solution of paclitaxel having improved stability.
CROSS-REFERENCE TO RELATED FOREIGN APPLICATION
This application claims priority under 35 USC 119 to Australian Patent No. 6074 filed Nov. 27, 1992.
BACKGROUND OF THE INVENTION
Paclitaxel is a compound extracted from the bark of a western yew, Taxus brevifolia and known for its antineoplastic activity. It is described for example in The Merck Index, Eleventh Edition 1989, monograph 9049.
In 1977, paclitaxel was chosen for development as an antineoplastic agent because of its unique mechanism of action and good cytotoxic activity against IP implanted D16 melanoma and the human X-1 mammary tumor xenograft. Paclitaxel is believed to function as a mitotic spindle poison and as a potent inhibitor of cell replication in vitro. Other mitotic spindle points (colchicine and podophyllotoxin) inhibit microtubule assembly. Paclitaxel employs a different mechanism of action since it appears to shift the equilibrium of polymerimization/depolymerization toward polymer assembly and to stabilize microtubules against depolymerization under conditions which would cause rapid disaggregation of microtubules. The interference with the polymerization/depolymerization cycle in cells appears to interfere with both the replication and migration of cells.
After extensive preclinical screening in mouse tumor models, paclitaxel entered clinical trials in 1983. Over the past few years, paclitaxel has demonstrated good response rates in treating both ovarian and breast cancer patients who were not benefitting from vinca alkaloid or cisplatin therapy. It has also shown encouraging results in patients with other types of cancer including lung, melanoma, lymphoma, head and neck.
For further information, reference may be made to the U.S. National Cancer Institute's Clinical Brochure for Taxol, revised July 1991, and papers presented at the Second National Cancer Institute Workshop on Taxol and Taxus held in Alexandria, Va. USA on Sep. 23-24, 1992.
BRIEF DESCRIPTION OF THE INVENTION
It is a disadvantage of the known formulation that the paclitaxel therein degrades, with the result that the shelf life of the formulation is unsatisfactory, and there is therefore a need for a paclitaxel solution of improved stability.
Accordingly, in a general aspect the invention provides a solution containing paclitaxel, cremophor EL™ and ethanol, characterized in that the pH of the solution has been adjusted into the range 1 to 8 by addition of an acid.
Acids in the form of powders, for example citric acid, are preferred over those which contain water, for example sulfuric acid. The most preferred acid for use in accordance with the present invention is citric acid, but a wide range of acids may be used including the following:
Citric acid—monohydrous
Citric acid—anhydrous
Citric acid—hydrous
Acetic acid
Formic acid
Ascorbic acid
Aspartic acid
Benzene sulphonic acid
Benzoic acid
Hydrochloric acid
Sulphuric acid
Phosphoric acid
Nitric acid
Tartaric acid
Diatrizoic acid
Glutamic acid
Lactic acid
Maleic acid
Succinic acid
DETAILED DESCRIPTION OF THE ILLUSTRATED EMBODIMENTS
Due to its limited solubility in water, Paclitaxel is usually prepared and administered in a vehicle containing cremophor EL™ (a polyethoxylated castor oil which acts as a solubilizer) and ethanol. A commercially available solution supplied by Bristol-Myers Squibb (BMS) is formulated with these components and has a pH of 9.1.
As indicated above, the invention essentially teaches addition of an acid to a paclitaxel formulation to adjust its pH into the range 1 to 8, preferable 5 to 7.
In a preferred procedure adopted by the applicant, which it will be clearly understood is non-limiting, the following steps were carried out:
Mixing Instructions
Solution 1
Citric acid was dissolved in absolute alcohol, using a ratio of 8 mls of absolute alcohol to 1 gram of citric acid, and the solution was stirred for fifteen (15) minutes.
Solution 2
Cremophor EL was weighed out into the main mixing vessel.
Solution 3
Solution 1 was added to solution 2, and the container used for solution 2 was washed with a minimum quantity of absolute alcohol to ensure complete transfer of the citric acid. Solution 3 was mixed and bubbled with nitrogen for at least 15 minutes. The paclitaxel was weighed out and slurried using absolute alcohol, using a ratio of 8 ml of absolute alcohol to 1 gm of paclitaxel. The slurried paclitaxel was added to solution 3 and the slurrying vessel was washed with a minimum quantity of absolute alcohol. Solution 3 was adjusted to 75% of required volume using absolute alcohol, and thoroughly stirred for at least 45 minutes until completely dissolved. Once completely dissolved, the volume was checked and made up as necessary with absolute alcohol and the final solution stirred for 5 minutes.
EXAMPLE 1
A solution was prepared with the following formulation:
Formulation: (Sample 1)
Cremophor EL 0.5 mL
Citric Acid (Anhydrous) 2.0 mg
Paclitaxel 6.0 mg
Absolute Alcohol to 1.0 mL
The pH of this solution was determined as 6.1.
The stability of this sample was compared with a sample prepared by the formulation stated in the NCI Taxol Clinical brochure (as follows) which had a pH of 9.1. (Sample 2)
Sample 2 per mL
Paclitaxel 6 mg
Cremophor EL 0.5 mL
Absolute Alcohol to 1 mL
The solutions were filled into clear type 1 glass 5 mL vials and sealed with rubber bungs.
The solutions were stored at 40° C. for 7 (seven) days and the stability results are shown in Table 1.
Sample 1 Sample 2
pH 6.2 9.0
Potency 96.6 86.7
Major individual impurity 0.3% 5.1%
Total impurities 1.0% 12.2%
Clearly Sample 1 showed significantly increased stability over Sample 2.
EXAMPLE 2
A solution was prepared with the following formulation:
Formulation: (Sample 3)
Cremophor EL 0.5 mL
Paclitaxel 6.0 mg
Absolute Ethanol to 1.0 mL
The solution was filled into clear type I glass 5 mL vials and sealed with rubber bungs.
The solution was stored at 40° C. for 7 days.
The stability results obtained are compared to those seen with Sample 2.
Sample 1 Sample 2
pH 6.7 9.0
Potency 97.5 86.7
Major individual impurity 0.3% 5.1%
Total impurities 2.3% 12.2%
Again the significantly superior stability of the formulation according to the invention (Sample 3) is evident.
It will be clearly understood that the invention in its general aspects is not limited to the specific details referred to hereinabove.

Claims (38)

What is claimed is:
1. A composition of matter comprising a sealable container and a pharmaceutical formulation contained therein; said pharmaceutical formulation comprising paclitaxel, a pharmaceutically-acceptable carrier, and an acid, said formulation being such that at least 95% of the paclitaxel potency is retained when said formulation is stored at 40° C. for seven days; and wherein said pharmateutical formulation has been sealed in said container for at least seven days.
2. A composition of matter produced by the process of:
a) obtaining a sealable container;
b) obtaining a pharmaceutical formulation comprising paclitaxel, a pharmaceutically-acceptable carrier, and an acid, said formulation being such that at least 95% of the paclitaxel potency is retained when said formulation is stored at 40° C. for seven days;
c) placing said pharmaceutical formulation in said sealable container;
d) sealing said sealable container; and
e) storing said pharmaceutical formulation in said sealed container for at least seven days.
3. A composition of matter according to claim 1, wherein said pharmaceutical formulation has a pH between 5 and 7, inclusive.
4. A composition of matter according to claim 1, further comprising ethanol as a constituent thereof.
5. A composition of matter according to claim 4, wherein said pharmaceutical formulation has a pH between 5 and 7, inclusive.
6. A composition of matter according to claim 1, wherein said pharmaceutically acceptable carrier is polyethoxylated castor oil.
7. A composition of matter according to claim 1, wherein said pharmaceutical formulation is anhydrous.
8. A composition of matter according to claim 6, wherein said acid is a mineral acid.
9. A composition of matter according to claim 6, wherein said acid is an organic acid.
10. A composition of matter according to claim 6, wherein said acid is acetic acid.
11. A composition of matter according to claim 6, wherein said acid is citric acid.
12. A composition of matter according to claim 11, wherein said citric acid is anhydrous.
13. A composition of matter according to claim 2, wherein said pharmaceutical formulation has a pH between 5 and 7, inclusive.
14. A composition of matter according to claim 2, further comprising ethanol as a constituent thereof.
15. A composition of matter according to claim 14, wherein said pharmaceutical formulation has a pH between 5 and 7, inclusive.
16. A composition of matter according to claim 2, wherein said pharmaceutically acceptable carrier is polyethoxylated castor oil.
17. A composition of matter according to claim 2, wherein said pharmaceutical formulation is anhydrous.
18. A composition of matter according to claim 16, wherein said acid is a mineral acid.
19. A composition of matter according to claim 16, wherein said acid is an organic acid.
20. A composition of matter according to claim 16, wherein said acid is acetic acid.
21. A composition of matter according to claim 16, wherein said acid is citric acid.
22. A composition of matter according to claim 21, wherein said citric acid is anhydrous.
23. A method of formulating a pharmaceutical paclitaxel composition such that the paclitaxel does not readily degrade, comprising the following steps:
mixing paclitaxel with a pharmaceutically acceptable carrier material to form a pharmaceutical paclitaxel composition, the pH of said carrier material having been reduced to a level such that when paclitaxel is mixed therewith at least 95% of the paclitaxel potency is retained when the composition is stored at 40° C. for seven days;
sealing said pharmaceutical paclitaxel composition in a sealable container; and
storing said pharmaceutical paclitaxel composition in said sealed container for at least seven days.
24. A method according to claim 23, wherein said pharmaceutically acceptable carrier material comprises polyethoxylated castor oil.
25. A method according to claim 23, wherein said pharmaceutical paclitaxel composition is anhydrous.
26. A method according to claim 24, wherein said pharmaceutical paclitaxel composition also comprises ethanol.
27. An article of manufacture comprising a container and a pharmaceutical formulation contained therein, said pharmaceutical formulation comprising a pharmaceutically acceptable carrier and paclitaxel, wherein the pH of said pharmaceutically acceptable carrier has been reduced to a level such that at least 95% of the potency of paclitaxel added thereto is retained when the pharmaceutical formulation is stored at 40° C. for seven days.
28. An article of manufacture according to claim 27, wherein said pharmaceutically acceptable carrier comprises polyethoxylated castor oil.
29. An article of manufacture according to claim 28, wherein said pharmaceutical formulation is anhydrous.
30. An article of manufacture according to claim 28, wherein said pharmaceutical formulation further comprises ethanol.
31. A method of making a pharmaceutical paclitaxel composition, comprising the steps of:
obtaining a pharmaceutically acceptable carrier material;
reducing the pH of said carrier material to a level such that when paclitaxel is mixed therewith, at least 95% of the paclitaxel potency is retained when the resulting composition is stored at 40° C. for seven days;
mixing paclitaxel with said reduced-pH carrier material to form a pharmaceutical paclitaxel composition;
sealing said pharmaceutical paclitaxel composition in a sealable container; and
storing said pharmaceutical paclitaxel composition in said sealed container for at least seven days.
32. A method according to claim 31, wherein said pharmaceutically acceptable carrier material comprises polyethoxylated castor oil.
33. A method according to claim 32 wherein said pharmaceutical paclitaxel composition is anhydrous.
34. A method according to claim 31, wherein said pharmaceutical paclitaxel composition further comprises ethanol.
35. A composition of matter produced by the process of:
obtaining a pharmaceutically acceptable carrier material;
reducing the pH of said carrier material to a level such that when paclitaxel is mixed therewith, at least 95% of the paclitaxel potency is retained when the resulting composition is stored at 40° C. for seven days;
mixing paclitaxel with said reduced-pH carrier material to form a pharmaceutical paclitaxel composition;
sealing said pharmaceutical paclitaxel composition in a sealable container; and
storing said pharmaceutical paclitaxel composition in said sealed container for at least seven days.
36. A composition of matter according to claim 35 wherein said pharmaceutically acceptable carrier material comprises polyethoxylated castor oil.
37. A composition of matter according to claim 36, wherein said pharmaceutical paclitaxel composition is anhydrous.
38. A composition of matter according to claim 35, wherein said pharmaceutical paclitaxel composition further comprises ethanol.
US09/563,969 1992-11-27 2000-05-03 Injectable composition Expired - Fee Related US6306894B1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US09/563,969 US6306894B1 (en) 1992-11-27 2000-05-03 Injectable composition
US09/970,558 US6770670B2 (en) 1992-11-27 2001-10-04 Injectable composition
US10/835,875 US20040204479A1 (en) 1992-11-27 2004-04-29 Injectable composition

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
AU6074 1984-07-18
AUPL607492 1992-11-27
US99550192A 1992-12-22 1992-12-22
US08/594,478 US5733888A (en) 1992-11-27 1996-01-31 Injectable composition
US08/979,836 US5977164A (en) 1992-11-27 1997-11-26 Stabilized pharmaceutical composition
US09/356,158 US6140359A (en) 1992-11-27 1999-07-19 Injectable composition
US09/563,969 US6306894B1 (en) 1992-11-27 2000-05-03 Injectable composition

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
US09/356,158 Continuation US6140359A (en) 1992-11-27 1999-07-19 Injectable composition

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US09/970,558 Continuation US6770670B2 (en) 1992-11-27 2001-10-04 Injectable composition

Publications (1)

Publication Number Publication Date
US6306894B1 true US6306894B1 (en) 2001-10-23

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ID=25644377

Family Applications (7)

Application Number Title Priority Date Filing Date
US08/594,478 Expired - Lifetime US5733888A (en) 1992-11-27 1996-01-31 Injectable composition
US08/979,836 Expired - Lifetime US5977164A (en) 1992-11-27 1997-11-26 Stabilized pharmaceutical composition
US09/028,906 Expired - Lifetime US5972992A (en) 1992-11-27 1998-02-24 Injectable composition
US09/356,158 Expired - Fee Related US6140359A (en) 1992-11-27 1999-07-19 Injectable composition
US09/563,969 Expired - Fee Related US6306894B1 (en) 1992-11-27 2000-05-03 Injectable composition
US09/970,558 Expired - Fee Related US6770670B2 (en) 1992-11-27 2001-10-04 Injectable composition
US10/835,875 Abandoned US20040204479A1 (en) 1992-11-27 2004-04-29 Injectable composition

Family Applications Before (4)

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US08/594,478 Expired - Lifetime US5733888A (en) 1992-11-27 1996-01-31 Injectable composition
US08/979,836 Expired - Lifetime US5977164A (en) 1992-11-27 1997-11-26 Stabilized pharmaceutical composition
US09/028,906 Expired - Lifetime US5972992A (en) 1992-11-27 1998-02-24 Injectable composition
US09/356,158 Expired - Fee Related US6140359A (en) 1992-11-27 1999-07-19 Injectable composition

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US09/970,558 Expired - Fee Related US6770670B2 (en) 1992-11-27 2001-10-04 Injectable composition
US10/835,875 Abandoned US20040204479A1 (en) 1992-11-27 2004-04-29 Injectable composition

Country Status (12)

Country Link
US (7) US5733888A (en)
EP (4) EP1384474A1 (en)
JP (1) JP2880292B2 (en)
AT (2) ATE169216T1 (en)
AU (1) AU5612694A (en)
CA (2) CA2149150C (en)
DE (2) DE69320206T2 (en)
DK (2) DK0835657T3 (en)
ES (2) ES2119996T3 (en)
GR (1) GR3027724T3 (en)
PT (1) PT835657E (en)
WO (2) WO1994012030A1 (en)

Cited By (8)

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Publication number Priority date Publication date Assignee Title
US20030207936A1 (en) * 2000-11-28 2003-11-06 Hongming Chen Pharmaceutical formulations comprising paclitaxel, derivatives, and pharmaceutically acceptable salts thereof
US20030220391A1 (en) * 2001-12-20 2003-11-27 Bogardus Joseph Ballard Pharmaceutical compositions of orally active taxane derivatives having enhanced bioavailability
US20040092428A1 (en) * 2001-11-27 2004-05-13 Hongming Chen Oral pharmaceuticals formulation comprising paclitaxel, derivatives and methods of administration thereof
US20040204479A1 (en) * 1992-11-27 2004-10-14 David Carver Injectable composition
US20050016926A1 (en) * 2003-07-24 2005-01-27 Dabur Research Foundation Stabilized formulation
US20050142225A1 (en) * 2002-06-10 2005-06-30 Pliva-Lachema A.S. Stabilised pharmaceutical compositions on the basis of polyoxyethlated castor oil and method for manufacturing the same
JP2006143699A (en) * 2004-11-24 2006-06-08 Yung Shin Pharmaceutical Industry Co Ltd Paclitaxel aqueous injection and method for preparing the same
US20110038926A1 (en) * 2002-06-26 2011-02-17 Medigene Oncology Gmbh Method of producing a cationic liposomal preparation comprising a lipophilic compound

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TW406020B (en) * 1993-09-29 2000-09-21 Bristol Myers Squibb Co Stabilized pharmaceutical composition and its method for preparation and stabilizing solvent
FR2710534B1 (en) * 1994-09-28 1996-07-05 Bristol Myers Squibb Co Stabilization solvent, pharmaceutical composition containing it, and process for its preparation.
NL9500340A (en) * 1995-02-22 1996-10-01 Yew Tree Pharmaceuticals B V Stabilized paclitaxel solution and pharmaceutical preparation containing said solution
DE19536165A1 (en) * 1995-09-28 1997-04-03 Basf Ag Process for cleaning alkoxylated fats
US6245805B1 (en) * 1995-10-26 2001-06-12 Baker Norton Pharmaceuticals, Inc. Method, compositions and kits for increasing the oral bioavailability of pharmaceutical agents
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